August aibert



Reissuecl Mar. 6, 1923.

.umrao STATES METHOD or PRODUCING PAT]; NT 1, j

"A GUs'r ALBERT, or Monica; G R ANY. y I

- wrrn' rarvarnnr ARS'ENIQ.

NEW Anomarro coniPoUNDs*oon'TAINrne caRBon*r GnouPs no Drawing. original Noa1,425,931,:idated August 15,"1922,Seria1 1'o. 546,794, medman-125, 19 221 Y Application iorreis sue filed January 5,, 1923. Serial Nora-610,900. i

To all whom it may 05mm.-

citizen of the Republic of Germany, andre siding at Munich, Germany, Elisabethstrasse 46, have inventedla new and useful Method of Producing New ;Aromatic Compounds Containing Carbonylgroups' with Trivalent Arsenic, of which the following is a specification w p I It is well known that the carbonyl group in aldehydes'and ketones is very reactive and therefore aldehydes and ketonesreact very easily with reagents of'themost varied I nature. For example, it is generally known that these bodies can beeasily reduced by a great varietyof reducing agents. It is fur ther known that thc carbonyl group forms with bisulphites' and h drosulphites addition products which may e. regardedasesters. Another example 'of the reactivity of the carbonyl group is givenby Fossek (Wiener Monatschefte', vol. 5,-p. 625, andvol. 7, p. who shows that aldehydes, ketones, acid amids, etc, form phosphonic acids.

I have now discovered that it is possible tovsubject arsenic compounds such as those of the aromatic series which contain one or more carbonyl groups in non-cyclic linkage with an arsonic acid nucleus, to reduction in such manner that the arsenic group only is reduced. By the term carbonyl group in non-cyclic linkage, I mean, a carbonyl group contained 1n a sidechain. In thls manner,

for example arsonic acids of the type- RAs=O H where R is an aromatic group containing one or more carbonyl groups, are reduced to the correspondlng oxides ami o,

sodium bisulfite and the like are especially adapted.

The new substance containing trivalent arsenic produced in the aforesaid manner possesses valuable therapeutic properties and from it can be prepared derivatives which are effective in the control of the i trypanomiasz's and the B aicillus sprroclidsfici" Be it knownthat I, AUGUST .ALBERT, a,

palh'da; .To, illustrate different .methodsof practising my invention the following examples are given. v r 1'. 5 grams benzaldehyde arsonic acid con.

asolution of 50 gms. sodium hydrosulphite and 10 gms. chloride of magnesia in 200- ccm. of water .an-d this mixture is stirred 1% to 2 hours at a temperature. of about 60 (1.

, The desired arseno bennaldehydebseparates out, It is then filtered by suction and washed and dried in .vacuo. The resulting product hasa dark col or, i decompos'es at about v f '1 WI 2. 6.6 gms. 1-oxy-6-nitro-2]butyro-Par sonic acid are dissolved in ccm. normal 1 NaOH, which solution is diluted with 70.ccm.'water..

lution of 13 gms. chloride'of magnesium and 76 grams of sodium hydrosulfite 'in' 330 ccm. water. It is stirred at a' temperature of about 60 for 1 to 1-} hours. The precipitate is filtered with suction, washed. and dried in vacuo. The arsenovbenzol so obtained grad: ually darkens ing. y 3. 1 gm. p-acetonphenonarsonic acid-is coon,

iss oils I- i poured intoa solution of 5'ccm. sodium bis sulphite.x By heating with a'free flame the substance is for a moment dissolved but "thenat once the separation of the arsenic at about 10Q C. without -melt- This solution is. added with stirring to a so- V bel?dissolved"rbyz iaddit ion ofg- 'watery By means of a solution of ammonium":chloride a the arsenic oxide can be separated again out oxide be ins. The reaction is completed by heatinfi "p half-fami -hgur 'onztheiwater bajh. It is"theii*tfilteredwith suction-,-washedand dried on a .piece of porous earthenware. The arsenic oxide formsqa sedium saltdiifi, cult to dissolve in normal NaOHfbut it may cipitate. The-oxiddeomposes at aitemper-u 7 350,11 arsenic acidis dissolved; in 24 com. Water and 8,8 ccm. normal sodium hydrate and filtered. 0.4 gm. potassium iodideand 16.00111.

e stream? "aboutlil' "hour,' me anwhil 'coolin' "*the s'olution with water: Theniixtnre t ailotv'edto IfGmain-inthe-VesSeIfOr-QA the arsenic bxidsd produced is then fiiterd with suction fend dried on a; piece of ated by a 'solutibn of At a temperamremf 230t0 235"" "the arsenicexMe djcofm;

po e o d rkb wn m with sodium hydrosulphite an aromatic group-'attached to the benzolring. I

3*. AS a new comptauud;- aisubstance containing-ithe group R=Aa in which Broomp'rises an "aromatic group} to- Which is 1 atmehedaaycaibe yr grou v 4: "Asa newaeompound, 1-4 ars'eno ban! zaldehyde of the general structure:

dgn

I testimony whereof I have signed-f In name-"to thisfspe'cificatibn in the:pre's-ji-jnce of two .subscrihing Witneses:

i AUGUST 1 '"\Witness'es':' I

AL xaNnnnmniSoTo,

Pin-amen. 

